Amide condensation using arylboronic acid catalysts is heretofore known. For example, Patent Literature 1, on page 39, describes arylboronic acid catalysts such as 2-(diisopropylaminomethyl)phenylboronic acid and 2-(2,2,6,6-tetramethylpiperidinylmethyl)phenylboronic acid, and, on pages 42 and 43, describes a reaction example in which a carboxylic acid compound and an amine compound are subjected to amide condensation catalyzed by 2-(diisopropylaminomethyl)phenylboronic acid to give the corresponding carboxylic acid amide compound.
Further, in Non Patent Literature 1, a reaction example is described in which the amide condensation between a carboxylic acid compound and an amine compound is catalyzed by 3,4,5-trifluorophenylboronic acid that is an arylboronic acid compound having an electron-withdrawing substituent to produce the corresponding carboxylic acid amide compound. For example, a carboxylic acid amide compound substantially free from racemization is shown to be obtained in high yield by the amide condensation between an optically active α-hydroxycarboxylic acid compound and benzylamine under toluene reflux.